WO2018155547A1 - 感光性樹脂組成物、硬化パターンの製造方法、硬化物、層間絶縁膜、カバーコート層、表面保護膜、及び電子部品 - Google Patents

感光性樹脂組成物、硬化パターンの製造方法、硬化物、層間絶縁膜、カバーコート層、表面保護膜、及び電子部品 Download PDF

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Publication number
WO2018155547A1
WO2018155547A1 PCT/JP2018/006424 JP2018006424W WO2018155547A1 WO 2018155547 A1 WO2018155547 A1 WO 2018155547A1 JP 2018006424 W JP2018006424 W JP 2018006424W WO 2018155547 A1 WO2018155547 A1 WO 2018155547A1
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Prior art keywords
component
group
resin composition
photosensitive resin
mass
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PCT/JP2018/006424
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English (en)
French (fr)
Japanese (ja)
Inventor
伸行 斉藤
由香里 鯉渕
生田目　豊
Original Assignee
日立化成デュポンマイクロシステムズ株式会社
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Application filed by 日立化成デュポンマイクロシステムズ株式会社 filed Critical 日立化成デュポンマイクロシステムズ株式会社
Priority to KR1020197022433A priority Critical patent/KR102646304B1/ko
Priority to JP2019501408A priority patent/JP7095676B2/ja
Priority to US16/487,948 priority patent/US11226560B2/en
Priority to CN201880013138.1A priority patent/CN110325912B/zh
Publication of WO2018155547A1 publication Critical patent/WO2018155547A1/ja
Priority to PH12019501809A priority patent/PH12019501809A1/en
Priority to JP2022092957A priority patent/JP7294503B2/ja

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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004—Photosensitive materials
    • G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/032—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders
    • G03F7/037—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with binders the binders being polyamides or polyimides
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
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    • H01L21/00—Processes or apparatus adapted for the manufacture or treatment of semiconductor or solid state devices or of parts thereof
    • H01L21/02—Manufacture or treatment of semiconductor devices or of parts thereof
    • H01L21/02104—Forming layers
    • H01L21/02107—Forming insulating materials on a substrate
    • H01L21/02109—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates
    • H01L21/02112—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer
    • H01L21/02118—Forming insulating materials on a substrate characterised by the type of layer, e.g. type of material, porous/non-porous, pre-cursors, mixtures or laminates characterised by the material of the layer carbon based polymeric organic or inorganic material, e.g. polyimides, poly cyclobutene or PVC
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
    • C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
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    • G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
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    • G03F7/2002—Exposure; Apparatus therefor with visible light or UV light, through an original having an opaque pattern on a transparent support, e.g. film printing, projection printing; by reflection of visible or UV light from an original such as a printed image
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    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
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Definitions

  • the present invention relates to a photosensitive resin composition, a method for producing a cured pattern, a cured product, an interlayer insulating film, a cover coat layer, a surface protective film, and an electronic component.
  • a protective film (cured film) using such a polyimide resin is obtained by heating and curing a resin film formed by applying and drying a polyimide precursor or a resin composition containing a polyimide precursor on a substrate. It is obtained with.
  • a resin composition capable of forming various pattern shapes (pattern profiles) is required.
  • Various proposals have been made for the photosensitive agent contained in the resin composition in order to cope with higher resolution, and a highly sensitive photosensitive agent may be used (for example, Patent Document 1).
  • An object of the present invention is to provide a photosensitive resin composition having excellent handleability and capable of easily controlling a pattern profile.
  • the photosensitive resin composition containing the following (a) component, (b1) component, and (b2) component.
  • R 1 is a tetravalent organic group
  • R 2 is a divalent organic group
  • R 3 and R 4 are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, or carbon.
  • R 11 is an alkyl group having 1 to 12 carbon atoms, and a is an integer of 0 to 5.
  • R 12 is a hydrogen atom or an alkyl group having 1 to 12 carbon atoms.
  • R 13 And R 14 each independently represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a phenyl group or a tolyl group.
  • R 15 is —OH, —COOH, —O (CH 2 ) OH, —O (CH 2 ) 2 OH, —COO (CH 2 ) OH or —COO (CH 2 ) 2 OH.
  • R 16 and R 17 are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 4 to 10 carbon atoms, a phenyl group, or a tolyl group.
  • b is an integer of 0 to 5.
  • R 21 is an alkyl group having 1 to 12 carbon atoms
  • R 22 and R 23 are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms.
  • a cycloalkyl group having 4 to 10 carbon atoms, a phenyl group or a tolyl group, and c is an integer of 0 to 5.
  • R 24 and R 25 are each independently an alkyl group having 1 to 12 carbon atoms, d and e are each independently an integer of 0 to 5, and s and t are each independently 0 to It is an integer of 3, and the sum of s and t is 3. ) 2.
  • the content of the component (b1) is 0.05 to 5.0 parts by mass with respect to 100 parts by mass of the component (a), and the content of the component (b2) is 100 parts by mass of the component (a).
  • the photosensitive resin composition according to 1 or 2 which is 0.5 to 10.0 parts by mass. 4).
  • FIG. 1 is a schematic cross-sectional view of a semiconductor device having an interlayer insulating film, a cover coat layer, and a surface protective film according to an embodiment of the present invention.
  • the photosensitive resin composition of this invention the manufacturing method of a hardening pattern, hardened
  • the present invention is not limited to the following embodiments.
  • “A or B” may include either one of A or B, or may include both.
  • the material illustrated below may be used individually by 1 type, and may be used in combination of 2 or more type.
  • the content of each component in the photosensitive resin composition is such that when there are a plurality of substances corresponding to each component in the photosensitive resin composition, unless otherwise specified, Means the total amount of the plurality of substances present.
  • process is not limited to an independent process, and is included in the term if the intended action of the process is achieved even when it cannot be clearly distinguished from other processes.
  • the numerical range indicated by using “to” indicates a range including the numerical values described before and after “to” as the minimum value and the maximum value, respectively.
  • (Meth) acryloxy” represents “methacryloxy” or “acryloxy”
  • (meth) acrylate” represents “methacrylate” or “acrylate”.
  • the photosensitive resin composition of this invention contains the following (a) component, (b1) component, and (b2) component.
  • R 1 is a tetravalent organic group
  • R 2 is a divalent organic group
  • R 3 and R 4 are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, or carbon.
  • R 11 is an alkyl group having 1 to 12 carbon atoms, and a is an integer of 0 to 5.
  • R 12 is a hydrogen atom or an alkyl group having 1 to 12 carbon atoms.
  • R 13 And R 14 each independently represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a phenyl group or a tolyl group.
  • R 15 is —OH, —COOH, —O (CH 2 ) OH, —O (CH 2 ) 2 OH, —COO (CH 2 ) OH or —COO (CH 2 ) 2 OH.
  • R 16 and R 17 are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a cycloalkyl group having 4 to 10 carbon atoms, a phenyl group, or a tolyl group.
  • b is an integer of 0 to 5.
  • R 21 is an alkyl group having 1 to 12 carbon atoms
  • R 22 and R 23 are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or an alkoxy group having 1 to 12 carbon atoms.
  • a cycloalkyl group having 4 to 10 carbon atoms, a phenyl group or a tolyl group, and c is an integer of 0 to 5.
  • R 24 and R 25 are each independently an alkyl group having 1 to 12 carbon atoms, d and e are each independently an integer of 0 to 5, and s and t are each independently 0 to It is an integer of 3, and the sum of s and t is 3.
  • the photosensitive resin composition of the present invention is preferably a negative photosensitive resin composition.
  • the photosensitive resin composition of the present invention can be applied by combining a specific high-sensitivity photosensitizer with a specific standard-sensitivity photosensitizer as compared with the case where only the high-sensitivity photosensitizer is used.
  • the range (margin) can be greatly expanded, that is, the handleability can be greatly improved.
  • the photosensitive resin composition of the present invention has a gradual change in pattern profile that accompanies increase / decrease in the amount of photosensitive agent added, and a desired pattern profile can be easily obtained.
  • the component (a) is a polyimide precursor having a structural unit represented by the following formula (1).
  • R 1 is a tetravalent organic group
  • R 2 is a divalent organic group
  • R 3 and R 4 are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, or carbon.
  • R 1 in the formula (1) is a structure derived from a tetracarboxylic acid used as a raw material or a dianhydride thereof.
  • a raw material corresponding to R 1 known materials can be used without particular limitation.
  • the tetravalent organic group of R 1 is preferably any one of groups represented by the following formulas (2a) to (2e) from the viewpoint of reducing the stress of the cured film. You may use these individually or in combination of 2 or more types.
  • X and Y each represent a divalent group or a single bond that is not conjugated to a benzene ring that is independently bonded.
  • Z is an ether bond (—O—) or a sulfide bond (—S—).
  • the “divalent group that is not conjugated with the benzene ring to be bonded” of X and Y in the formula (2d) is, for example, —O—, —S—, or a divalent group represented by the following formula.
  • R 5 is a carbon atom or a silicon atom.
  • R 6 is each independently a hydrogen atom or a halogen atom such as a fluorine atom.
  • the raw materials corresponding to R 1 include 3,3 ′, 4,4′-benzophenone tetracarboxylic dianhydride, 1,2,5,6-naphthalene tetracarboxylic dianhydride, 2,3,5 , 6-pyridinetetracarboxylic dianhydride, 1,4,5,8-naphthalenetetracarboxylic dianhydride, 3,4,9,10-perylenetetracarboxylic dianhydride, m-terphenyl-3, 3 ', 4,4'-tetracarboxylic dianhydride, p-terphenyl-3,3', 4,4'-tetracarboxylic dianhydride, 1,1,1,3,3,3-hexa Fluoro-2,2-bis (2,3-dicarboxyphenyl) propane dianhydride, 1,1,1,3,3,3-hexafluoro-2,2-bis (3,4-dicarboxyphenyl) Propane dianhydride, 2,2-bis (2,
  • R 2 in formula (1) is a structure derived from a diamine compound used as a raw material.
  • the divalent organic group of R 2 is preferably a divalent organic group represented by the following formula (5) from the viewpoint of i-line transmittance.
  • R 30 to R 37 are each independently a hydrogen atom, a fluorine atom or a monovalent organic group, and at least one of R 30 to R 37 is a fluorine atom or a monovalent organic group. .
  • Examples of the monovalent organic group represented by R 30 to R 37 include an alkyl group having 1 to 10 carbon atoms (preferably 1 to 6 carbon atoms) (for example, a methyl group) and 1 to 10 carbon atoms (preferably 1 to 6 carbon atoms). And a fluorinated alkyl group (for example, trifluoromethyl group).
  • the divalent organic group of R 2 is more preferably a divalent organic group represented by the formula (6) from the viewpoints of i-line transmittance and availability.
  • R 38 and R 39 are each independently a fluorine atom, a methyl group or a trifluoromethyl group.
  • R 2 is represented by the formula (5) or the formula (6) with respect to all the structural units represented by the formula (1).
  • the proportion of the structural unit that is a valent organic group may be 1 to 100 mol%, 10 to 100 mol%, or 30 to 100 mol%.
  • R 2 is a divalent organic group represented by the formula (5) or (6)
  • 2,2′-dimethylbenzidine 2,2′-bis (trifluoromethyl) -4
  • examples include 4′-diaminobiphenyl, 2,2′-bis (fluoro) -4,4′-diaminobiphenyl, 4,4′-diaminooctafluorobiphenyl, and the like.
  • R 2 is a divalent organic group other than the divalent organic group represented by the formula (5) or (6)
  • a corresponding diamine compound may be used, and as such a diamine compound,
  • R 2 is divalent represented by the formula (5) or (6) with respect to all the structural units represented by the formula (1).
  • the proportion of structural units that are divalent organic groups other than these organic groups may be 1 to 100 mol%, 10 to 100 mol%, or 30 to 100 mol%.
  • R 3 and R 4 in the formula (1) are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, or a monovalent organic group having a carbon-carbon unsaturated double bond.
  • alkyl group examples include methyl group, ethyl group, n-propyl group, 2-propyl group, n- Examples thereof include a butyl group, an n-hexyl group, an n-heptyl group, an n-decyl group, and an n-dodecyl group.
  • Examples of the cycloalkyl group include cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, adamantyl group and the like. Can be mentioned.
  • Examples of the monovalent organic group having a carbon-carbon unsaturated double bond include a (meth) acryloxyalkyl group in which the alkyl group has 1 to 10 carbon atoms.
  • Examples of the (meth) acryloxyalkyl group having 1 to 10 carbon atoms in the alkyl group include (meth) acryloxyethyl group, (meth) acryloxypropyl group, (meth) acryloxybutyl group and the like.
  • At least one of R 3 and R 4 is preferably an organic group having a carbon-carbon unsaturated double bond.
  • the molecular weight of the polyimide precursor represented by the formula (1) is preferably a weight average molecular weight in terms of polystyrene of 10,000 to 100,000, more preferably 15,000 to 100,000. More preferably, it is 20,000 to 85,000.
  • the weight average molecular weight is 10,000 or more, the stress after curing can be sufficiently reduced.
  • it is 100,000 or less, the solubility in a solvent is further improved, the viscosity of the solution is decreased, and the handleability can be further improved.
  • a weight average molecular weight can be measured by the gel permeation chromatography method, and can be calculated
  • the component (a) used in the present invention can be synthesized by a known method. For example, it can be synthesized by addition polymerization of tetracarboxylic dianhydride and a diamine compound.
  • the molar ratio of the tetracarboxylic dianhydride and the diamine compound is usually 1.0, but may be a molar ratio in the range of 0.7 to 1.3 for the purpose of controlling the molecular weight and the terminal residue.
  • the molar ratio is 0.7 to 1.3, the molecular weight of the obtained polyimide precursor can be made a certain level or more, and the low stress property after curing can be sufficiently expressed.
  • the content of the polyimide precursor may be 20 to 60% by mass, 25 to 55% by mass, or 30 to 55% by mass in the photosensitive resin composition.
  • the component (b1) and the component (b2) described later are a photosensitizer and usually generate radicals upon irradiation with actinic rays.
  • the component (b1) is, for example, a highly sensitive photosensitizer that has higher sensitivity to actinic rays than the component (b2) described later.
  • the component (b1) is one or more compounds selected from the group consisting of compounds represented by the following formula (11) and the following formula (12).
  • R 11 is an alkyl group having 1 to 12 carbon atoms
  • a is an integer of 0 to 5.
  • R 12 is a hydrogen atom or an alkyl group having 1 to 12 carbon atoms.
  • R 13 and R 14 each independently represent a hydrogen atom, an alkyl group having 1 to 12 carbon atoms (preferably 1 to 4 carbon atoms), a phenyl group or a tolyl group.
  • a is an integer of 2 or more, R 11 may be the same or different.
  • R 11 is preferably an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group. a is preferably 1.
  • R 12 is preferably an alkyl group having 1 to 4 carbon atoms, and more preferably an ethyl group.
  • R 13 and R 14 are preferably each independently an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group.
  • Examples of the compound represented by the formula (11) include a compound represented by the following formula (11-1), which is available as “IRGACURE OXE 02” manufactured by BASF Japan Ltd.
  • R 15 is —OH, —COOH, —O (CH 2 ) OH, —O (CH 2 ) 2 OH, —COO (CH 2 ) OH or —COO (CH 2 ) 2 OH.
  • R 16 and R 17 are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms (preferably 1 to 6 carbon atoms), a cycloalkyl group having 4 to 10 carbon atoms, a phenyl group, or a tolyl group.
  • b is an integer of 0 to 5. If b is an integer of 2 or more, R 15 may be the same or different.
  • R 15 is preferably —O (CH 2 ) 2 OH.
  • b is preferably 0 or 1.
  • R 16 is preferably an alkyl group having 1 to 6 carbon atoms, more preferably a methyl group or a hexyl group.
  • R 17 is preferably an alkyl group having 1 to 6 carbon atoms or a phenyl group, and more preferably a methyl group or a phenyl group.
  • Examples of the compound represented by the formula (12) include a compound represented by the following formula (12-1), and are available as “IRGACURE OXE 01” manufactured by BASF Japan Ltd.
  • compounds represented by the following formula (12-2) are listed, and are available as “NCI-930” manufactured by ADEKA Corporation.
  • the component (b2) is, for example, a photosensitizer having a standard sensitivity that is lower in sensitivity to actinic rays than the component (b1).
  • the component (b2) is one or more compounds selected from the group consisting of compounds represented by the following formula (21) and the following formula (22).
  • R 21 is an alkyl group having 1 to 12 carbon atoms
  • R 22 and R 23 are each independently a hydrogen atom, an alkyl group having 1 to 12 carbon atoms (preferably having 1 to 4 carbon atoms), An alkoxy group having 1 to 12 carbon atoms (preferably 1 to 4 carbon atoms), a cycloalkyl group having 4 to 10 carbon atoms, a phenyl group, or a tolyl group
  • c is an integer of 0 to 5.
  • R ⁇ 21 > may be same or different, respectively.
  • R 22 is preferably an alkyl group having 1 to 4 carbon atoms, and more preferably a methyl group.
  • R 23 is preferably an alkoxy group having 1 to 12 carbon atoms, more preferably an alkoxy group having 1 to 4 carbon atoms, and further preferably a methoxy group or an ethoxy group.
  • Examples of the compound represented by the formula (21) include a compound represented by the following formula (21-1), which is available as “G-1820 (PDO)” manufactured by Lambson.
  • R 24 and R 25 are each independently an alkyl group having 1 to 12 carbon atoms (preferably 1 to 4 carbon atoms), d and e are each independently an integer of 0 to 5; s and t are each independently an integer of 0 to 3, and the sum of s and t is 3.
  • R 24 may be the same or different.
  • e is an integer of 2 or more
  • R 25 may be the same or different.
  • s is an integer of 2 or more
  • the groups in parentheses may be the same or different.
  • t is an integer of 2 or more, the groups in parentheses may be the same or different.
  • R 25 is preferably each independently an alkyl group having 1 to 4 carbon atoms, preferably a methyl group.
  • e is preferably an integer of 2 to 4, more preferably 3.
  • the combination (s, t) of s and t is preferably (1, 2) or (2, 1).
  • Examples of the compound represented by the formula (22) include a compound represented by the following formula (22-1), and are available as “IRGACURE TPO” manufactured by BASF Japan Ltd. Moreover, the compound represented by the following formula (22-2) is mentioned, and it is available as “IRGACURE BAPO” manufactured by BASF Japan Ltd.
  • the content of the component (b1) in the photosensitive resin composition of the present invention is usually 0.05 to 5.0 parts by mass, preferably 0.05 to 1. parts by mass with respect to 100 parts by mass of the component (a). 0 parts by mass, more preferably 0.15 to 0.6 parts by mass.
  • the content of the component (b2) in the photosensitive resin composition of the present invention is usually 0.5 to 10.0 parts by mass, preferably 0.5 to 5. parts by mass with respect to 100 parts by mass of the component (a). 0 parts by mass.
  • the content of the component (b1) is 0.05 to 5.00 parts by mass with respect to 100 parts by mass of the component (a), and the content of the component (b2) with respect to 100 parts by mass of the component (a)
  • the amount is preferably 0.5 to 10.0 parts by mass.
  • the mass ratio of the content of the component (b1) and the component (b2) is preferably 1: 3 to 1:30, more preferably 1: 5 to 1:20.
  • the total amount of the component (b1) and the component (b2) in the photosensitive resin composition of the present invention is preferably 0.6 to 11.0 parts by mass, more preferably 100 parts by mass of the component (a).
  • the amount is 1.0 to 5.0 parts by mass, and more preferably 1.15 to 4.6 parts by mass.
  • the photosensitive resin composition of the present invention may consist essentially of components (a), (b1), (b2) and (c), or essentially consists of (a), (b1) and (b2). And (c) component and one or more components selected from other optional components described later.
  • the photosensitive resin composition of the present invention comprises only the components (a), (b1), (b2) and (c), or the components (a), (b1), (b2) and (c), and It may consist only of one or more components selected from other optional components.
  • the photosensitive resin composition of the present invention may contain an optional component as necessary in addition to the above components.
  • the optional component include a solvent (component (c)), a crosslinking agent (component (d)), a sensitizer (component (e)), an organic silane compound (component (f)), and other components.
  • dissolves the polyimide precursor which is (a) component fully is preferable, and polar Solvents include N-methyl-2-pyrrolidone (NMP), N, N-dimethylacetamide, N, N-dimethylformamide, dimethyl sulfoxide, tetramethylurea, hexamethylphosphate triamide, ⁇ -butyrolactone, ⁇ -valerolactone ⁇ -valerolactone, cyclohexanone, cyclopentanone, propylene glycol monomethyl ether acetate, propylene carbonate, ethyl lactate, 1,3-dimethyl-2-imidazolidinone and the like.
  • NMP N-methyl-2-pyrrolidone
  • the content of the component (c) in the photosensitive resin composition of the present invention is not particularly limited, but is preferably 50 to 300 parts by weight, more preferably 50 to 250 parts by weight with respect to 100 parts by weight of the component (a). 100 to 200 parts by mass is more preferable.
  • crosslinking agent different from (f) organosilane compound described later
  • examples of the crosslinking agent include diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, tetraethylene glycol di (meth) acrylate, and trimethylolpropane di (meth).
  • the content of the crosslinking agent is preferably 1 to 100 parts by mass, more preferably 1 to 75 parts by mass with respect to 100 parts by mass of the component (a). It is more preferable to set it as a mass part.
  • sensitizer examples include 7-N, N-diethylaminocoumarin, 7-diethylamino-3-thenonylcoumarin, 3,3′-carbonylbis (7-N, N-diethylamino) coumarin, and 3,3′-.
  • the content is more preferably 0.1 to 3.0 parts by mass, and 0.1 to 1.0 parts by mass with respect to 100 parts by mass of the (a) polyimide precursor. More preferably.
  • Organic silane compounds include ⁇ -aminopropyltrimethoxysilane, ⁇ -aminopropyltriethoxysilane, vinyltriethoxysilane, vinyltrimethoxysilane, ⁇ -glycidoxypropyltriethoxysilane, and ⁇ -glycidoxypropyltrimethoxy.
  • Silane ⁇ -methacryloxypropyltrimethoxysilane, ⁇ -acryloxypropyltrimethoxysilane, ⁇ -ureidopropyltriethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-isocyanatopropyltriethoxysilane, bis (2-hydroxyethyl) ) -3-Aminopropyltriethoxysilane, triethoxysilylpropylethylcarbamate, 3- (triethoxysilyl) propyl succinic anhydride, phenyltriethoxysilane, phenyltrimethoxy Silane, N-phenyl-3-aminopropyltrimethoxysilane, 3-triethoxysilyl-N- (1,3-dimethylbutylidene) propylamine, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, etc.
  • the content of the organosilane compound is more preferably 0.5 to 15 parts by mass, and 0.5 to 10 parts by mass with respect to 100 parts by mass of the component (a). Is more preferable.
  • the photosensitive resin composition of this invention may contain a rust preventive agent from a viewpoint of improving rust prevention property more.
  • the rust inhibitor include 5-amino-1H-tetrazole, 1-methyl-5-amino-tetrazole, 1-methyl-5-mercapto-1H-tetrazole, 1-carboxymethyl-5-amino-tetrazole and the like. . These tetrazole compounds may be water-soluble salts thereof.
  • the content is preferably 0.05 to 5.0 parts by mass, more preferably 0.5 to 4.0 parts by mass with respect to 100 parts by mass of the component (a).
  • the photosensitive resin composition of this invention may also contain a stabilizer.
  • a stabilizer a known compound such as 1,4,4-trimethyl-2,3-diazabicyclo [3.2.2] -non-2-ene-N, N-dioxoid can be used.
  • the content is preferably 0.05 to 5.0 parts by mass, more preferably 0.1 to 2.0 parts by mass with respect to 100 parts by mass of the component (a).
  • the cured product of the present invention can be obtained by curing the above-described photosensitive resin composition.
  • the cured product of the present invention may be used as a pattern cured film or a cured film having no pattern.
  • the film thickness of the cured product of the present invention is preferably 1 to 20 ⁇ m.
  • the method for producing a cured pattern of the present invention comprises a step of coating the photosensitive resin composition of the present invention on a substrate and drying to form a coating film (coating film forming process), and irradiating the formed coating film with actinic rays.
  • Examples of the method for applying the photosensitive resin composition on the substrate in the coating film forming step include an immersion method, a spray method, a screen printing method, and a spin coating method.
  • Examples of the substrate include a silicon wafer, a metal substrate, and a ceramic substrate.
  • the solvent is removed (dried) by heating to form a coating film (photosensitive resin film) with less adhesiveness.
  • the heating temperature for drying is preferably 80 to 130 ° C., and the drying time is preferably 30 to 300 seconds. Drying is preferably performed using an apparatus such as a hot plate.
  • the exposure step exposure is performed by irradiating the obtained coating film with actinic rays through a mask on which a desired pattern is drawn.
  • the photosensitive resin composition of the present invention is suitable for i-line exposure, ultraviolet rays, far ultraviolet rays, visible rays, electron beams, X-rays and the like can be used as the active rays to be irradiated.
  • a desired pattern can be obtained by dissolving and removing the unexposed portion with an appropriate developer in the development step.
  • the developer is not particularly limited, but is a flame retardant solvent such as 1,1,1-trichloroethane; N, N-dimethylformamide, dimethyl sulfoxide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, cyclohexane Good solvents such as pentanone, ⁇ -butyrolactone, and acetates; mixed solvents of these good solvents and poor solvents such as lower alcohols, water, and aromatic hydrocarbons are used.
  • rinsing with a poor solvent for example, water, ethanol, 2-propanol, PGMEA (propylene glycol 1-monomethyl ether 2-acetate)
  • a poor solvent for example, water, ethanol, 2-propanol, PGMEA (propylene glycol 1-monomethyl ether 2-acetate)
  • the heating temperature in the heat treatment step is preferably 250 ° C. or lower, and more preferably 230 ° C. or lower.
  • the heat treatment time is preferably 20 minutes to 6 hours, more preferably 30 minutes to 3 hours.
  • the thickness of the cured pattern of the present invention is preferably 1 ⁇ m or more, more preferably 5 ⁇ m or more for use as a protective film, and usually 20 ⁇ m or less.
  • the cured product (cured pattern) of the present invention can be used as an interlayer insulating film, a cover coat layer, a surface protective film, a rewiring layer, or the like.
  • These interlayer insulating film, cover coat layer, surface protective film and rewiring layer can be used for electronic components. Thereby, an electronic component with high reliability can be obtained.
  • the electronic component of the present invention can be used for semiconductor devices, multilayer wiring boards, and the like.
  • the semiconductor device and the multilayer wiring board can be used for various electronic devices.
  • the electronic component of the present invention is not particularly limited except that it has one or more selected from the above-described interlayer insulating film, cover coat layer, surface protective film, and rewiring layer, and can have various structures.
  • FIG. 2 shows a schematic cross-sectional view of a semiconductor device having an interlayer insulating film, a cover coat layer, and a surface protective film of the present invention.
  • An Al wiring layer 2 is formed on the interlayer insulating layer (interlayer insulating film) 1, an insulating layer (insulating film) 3 (for example, a P-SiN layer) is further formed on the Al wiring layer 2, and a surface protective layer of the device A (surface protective film) 4 is formed.
  • a rewiring layer 6 is formed from the pad portion 5 of the Al wiring layer 2 and extends to an upper portion of the core 8 which is a connection portion with a conductive ball 7 formed of solder, gold or the like as an external connection terminal. .
  • a cover coat layer 9 is formed on the surface protective layer 4.
  • the rewiring layer 6 is connected to the conductive ball 7 through the barrier metal 10, and a collar 11 is provided to hold the conductive ball 7.
  • an underfill 12 may be interposed in order to further relieve stress.
  • the weight average molecular weight of the polymer 1 was calculated
  • required by GPC method standard polystyrene conversion, and was measured on condition of the following. The measurement was performed using a solution of 1 mL of a solvent [tetrahydrofuran (THF) / N, N-dimethylformamide (DMF) 1/1 (volume ratio)] to polymer 1 (0.5 mg).
  • the weight average molecular weight of Polymer II was determined by GPC standard polystyrene conversion and measured under the same conditions as in Production Example 1.
  • Examples 1 to 17 and Comparative Examples 1 to 6 [Preparation of photosensitive resin composition] Photosensitive resin compositions of Examples 1 to 17 and Comparative Examples 1 to 6 were prepared with the components and blending amounts shown in Table 1. The compounding quantity of Table 1 is a mass part of each component with respect to 100 mass parts of (a) component. Each component used is as follows.
  • [(B1) component] B1-1 Compound having the following structure (trade name “IRGACURE OXE 02” manufactured by BASF Japan Ltd.)
  • [(B2) component] B2-1 Compound having the following structure (trade name “G-1820 (PDO)” manufactured by Lambson)
  • D-1 Compound having the following structure (trade name “TEGDMA”, manufactured by SARTOMER)
  • D-2 Compound having the following structure (manufactured by Shin-Nakamura Chemical Co., Ltd., trade name “A-TMMT”) C— (CH 2 OOC—CH ⁇ CH 2 ) 4
  • E-1 Compound having the following structure (trade name “EMK” manufactured by Aldrich) (Et represents an ethyl group)
  • Taobn 1,4,4-trimethyl-2,3-diazabicyclo [3.2.2] -non-2-ene-N, N-dixoid (product name “Taobn” manufactured by Hampford Research)
  • 5ATz Compound having the following structure (trade name “5-amino-1H-tetrazole”, manufactured by Tokyo Chemical Industry Co., Ltd.)
  • the taper angle can be easily adjusted by appropriately adjusting the addition amount and the mixing ratio. Can do. Moreover, the change in the pattern profile accompanying the increase / decrease of the addition amount was gradual, and the desired pattern profile was easily obtained.
  • the obtained photosensitive resin composition was applied onto a 6-inch silicon wafer by spin coating, heated on a hot plate at 110 ° C. for 4 minutes to volatilize the solvent, and a coating film having a thickness of 13 ⁇ m was obtained.
  • the development time was set to twice the time until complete dissolution.
  • the exposure dose range (referred to as “optimal exposure dose range”) at which a high resolution of 10 ⁇ m or less was obtained was small.
  • the photosensitive resin composition of the present invention uses the high-sensitivity photosensitizer and the standard-sensitivity photosensitizer in combination, so that the optimum exposure range is compared with the case where only the same amount of the high-sensitivity photosensitizer is used. Became bigger.
  • the optimum exposure dose range is 300 to 700 mJ / cm 2 (Comparative Example 4), but in addition to the same amount of the component (b1) ( When the component b2) was used, the optimum exposure dose range was at least 200 to 800 mJ / cm 2 (Example 9), and the maximum was 200 to 1100 mJ / cm 2 (Example 11), and the handleability was greatly improved.
  • the optimum exposure dose range of Example 15 is 200 to 400 mJ / cm 2 , but this is due to the characteristics of polymer II, and the optimum exposure dose range when combining only the component (b1) with polymer II is It is thought to be even smaller.
  • the optimal exposure amount range reached a certain level or more by setting the content of the component (b1) to 0.3 parts by mass or less, it was found that the handleability of the photosensitive resin composition was excellent.
  • the film thickness after image development was measured about the part which has not formed the pattern in the resin pattern.
  • the Example which uses the (b1) component and the (b2) component together provides a high remaining film ratio of 80% or more as compared with the comparative example using only the same amount of the (b1) component. It can be seen that the exposure range is wide.
  • the component (b1) is 0.3 parts by mass or more with respect to 100 parts by mass of the component (a)
  • the photosensitive resin composition of the present invention can be suitably used as a protective film material or pattern film forming material for electronic parts such as semiconductor devices.

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PCT/JP2018/006424 2017-02-23 2018-02-22 感光性樹脂組成物、硬化パターンの製造方法、硬化物、層間絶縁膜、カバーコート層、表面保護膜、及び電子部品 WO2018155547A1 (ja)

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